Jay Contessa
I am a third generation Ridgefield native currently living in Redding for over 25 years. I bring decades of local expertise on our awarded winning school systems and the distinct characteristics that make our communities so special. Our towns are graced with an abundance of scenic charm and family businesses with long held traditions of generosity and support. Fairfield County’s vast architecture of homes, proximity to NYC, the Vermont mountains, and to the shoreline, makes our communities the perfect choice to raise a family or for a weekend getaway.I bring a strong proven track record of negotiation skills, marketing, financing and customer service from my prior successful years in corporate leadership. In addition, I have personal experience in home building and complex renovations including residential and commercial properties. As a realtor, my role will be to facilitate and educate my clients to make the best decisions in what could be a complicated process of buying and selling homes.Today, you need a broker that knows the community's and has the professional resources and marketing tools to get the job done. I look forward to making that happen.
21
Closed Sales
$14.5M
Total Value
$3.2K - $2M
Price Range
$688.8K
Average Price
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SOLD/OFF MARKET LISTINGS
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Easton CT Home for Sale
Escape the city, and enjoy the beautiful town of Easton. Surround yourself with serenity and nature. Enjoy local farms, fresh fruit stands, apple picking, and hay rides. Three acres allow you to enjoy the quiet and fresh air. A little tlc can transition this house into a forever home.
❮❯Closed$549,999 Closed- 3 bds
- 2 ba
- 3330 sqft
10 Everett Road
Easton, CT
Listing by: Greg Kapetaneas - APHS Real Estate, LLC -
Redding CT Home for Sale
FABULOUS Colonial Reproduction home set on nearly 3 gorgeous acres of land. This picturesque property is located on a sought after scenic road, so close to Redding Center, award winning Redding schools and commuter roads/Metro North train. Originally built in 1939, this home has been completely renovated and expanded - MOVE IN READY! The heart of the home is the amazing kitchen! You'll love the high ceilings, wood burning fireplace with heat insert, honed slate counters, deep farm sinks, refrigerator drawers, stainless appliances and the beautiful variegated wide plank oak flooring. The 1st floor boasts a spacious Great Room (current Owner using as home office) & Family Room plus the original house front rooms w/chestnut flooring, hand hewn beams & butler's pantry - ALL with wood burning fireplaces! The 2nd floor has 5 bedrooms w/separate laundry room & back staircase. Enjoy the fireplace in the master bedroom & the renovated dual sink bathroom with private dressing room & plenty of built-ins for your clothing & accessories. Bonus: HUGE walk up attic and 2 lower level basements provide plenty of storage space. Above the 2 car detached garage you'll find a vaulted ceiling 20 x 20 unfinished space - perfect for a home office/half bath (Permits already approved by the Town of Redding) - Ready for the next Owner to easily finish! Gorgeous grounds with flowering gardens, stonewalls, and plenty of outdoor entertaining space on the brick patio. A Redding BEAUTY!
❮❯Closed$899,900 Closed- 5 bds
- 4 ba
- 3492 sqft
18 Great Pasture Road
Redding, CT
Listing by: Diane Millas - William Raveis Real Estate -
Redding CT Land for Sale
Level and ready lot to got. Approved septic plan. Seller has plans for a five bedroom house but you can create and build your own dream house. Seller is happy to answer any questions. Seller bought property and removed existing small house to create his own dream house but decided to purchase an already built property. Original small house on property has been removed.
❮❯Closed$250,000 Closed- bds
- 0 ba
- sqft
37 Whortleberry Road
Redding, CT
Listing by: Gerry Nusbaum - Brown Harris Stevens -
Norwalk CT Home for Sale
The charm of this antique farmhouse features all of the updates and conveniences of todays lifestyle including an electric car charging station! The open kitchen with granite counters, stainless steel appliances, including a gas range, is open to the dining area. Enter the living room with the fireplace as the center piece. A perfect cozy spot to relax or entertain guests. Off the living room is the first-floor bedroom, which is the perfect spot for a home office. Upstairs is the primary bedroom with an updated full bath and walk-in closet. The outdoor space is beyond compare with a babbling brook and charming bridge that spans the brook, a vegetable garden, a patio made of riverbed bluestones and theres even the original sharpening stone from the 1840s! Improvements include conversion to a propane gas HVAC system, new water heater, remodeled bathroom, refurbished fireplace, new gutters and partial roof, fencing and an electric car charger. Own a piece of history in this charming character filled home in Cranbury.
❮❯Closed$407,000 Closed- 2 bds
- 1 ba
- 1062 sqft
19 Grumman Avenue
Norwalk, CT
Listing by: Jane Walters - William Pitt Sotheby's Int'l -
Redding CT Land for Sale
A beautiful lot with a great views for your new home. Possible access options and more.
❮❯Closed$275,000 Closed- bds
- 0 ba
- sqft
234 Redding Road
Redding, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Ridgefield CT for Rent
Classic 4,452 SF 5 Bedroom Colonial located on 2 beautifully manicured acres featuring a level lot surrounded by trees, gardens and stone walls. This historic home features four finished floors, wide plank hardwood flooring, high ceilings, sun filled rooms and three large fireplaces. Main level offers a front foyer with field stone fireplace, large eat-in kitchen, office with built-ins, formal dining room and large living room with French doors to the salt water pool and patio. A Master En-Suite with fireplace, Juliet Balcony and beautiful renovated bathroom plus two nice sized guest bedrooms and hall bath complete the second floor and the third floor has two additional bedrooms and full bath. Lower level is complete with a large finished room with double viewing fireplace, a separate work shop and plenty of storage. Outside boasts gardens, salt water heated Gunite pool/spa and waterfall feature. Located mere minutes to downtown Ridgefield where you will find great Restaurants, shopping, theater, gyms and so much more!
❮❯Closed$10,000 Closed- 5 bds
- 4 ba
- 3752 sqft
22 Ashbee Lane
Ridgefield, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Redding CT Home for Sale
Welcome to the Georgetown Cottage & Gardens! Totally private & serene yet just a few minute walk to Georgetown village shops, restaurants, bars & more. This hidden gems boasts numerous updates (see attachments), offers five rooms plus a sunroom & partially finished basement all surrounded by gorgeous, thriving gardens in a fully-fenced yard. Though the lot (and taxes) are small, you're surrounded by dozens of acres of protected woods, making you feel like you're in the middle of a lush forest. The home features hardwood floors and amazing gardens views from almost every room. Have you been searching for a condo alternative with charm & style? Downsizing to a more manageable size home yet want to still have a beautiful, private yard? Please schedule a visit, you'll love what you find!
❮❯Closed$375,000 Closed- 2 bds
- 1 ba
- 1021 sqft
60 Portland Avenue
Redding, CT
Listing by: Chris Sinatra - Higgins Group Real Estate -
Easton CT Home for Sale
September 5th 2021 NY Times "On the Market" feature Home: This charming move in ready 1940s Salt box has been completely renovated. Complete with over $200,000 in updates and renovations to include a new septic system, windows, kitchen, HVAC, painting, deck/patio, spray foam insulation and a spectacular landscaping design and installation. This house is a must see! Over the last 5 years the owners have completely renovated this home and after expanding their family are moving to a new space in Easton. The first floor of this home flows beautifully with its formal dining area, fantastic updated kitchen, large living room with wood burning fireplace, and a bonus room which would make for a great home office or playroom. This bright cheery home has lots of windows, and 3 good sized bedrooms plus it is in a charming location with beautiful property making it an unparalleled listing at this price. The neighborhood path is steps away from our backyard and leads to the New Friends Playground, Sherwood Farm, Helen Keller Middle School, The Easton Community Center, local dog park, and tennis courts. The very best of Easton is right in your backyard! Just minutes to downtown Fairfield, restaurants, shopping, Sacred Heart and Fairfield U, and quick access to Merritt Parkway.
❮❯Closed$530,000 Closed- 3 bds
- 2 ba
- 1276 sqft
322 Sport Hill Road
Easton, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Ridgefield CT Home for Sale
As you head north from Ridgefield’s famous Main St, through the rolling hills of its equestrian farms, you’ll turn into a quiet neighborhood of high-end homes, drive along the golf course to the cul-de-sac and find stone pillars gracing the entrance of this ultimate entertainer’s home. Offering unparalleled luxury and space, the 7,110 sq feet on the first two floors are graced with custom millwork, Wainscoting, 10ft tray ceilings and exquisite hardwood floors. The large family room with fireplace and walls of windows is the center of entertainment, as it opens to the gourmet kitchen, featuring Wolf, Viking, SubZero, custom cabinetry and a 10ft granite island. Dinner parties of 20+ can also sit around one table in the formal dining room. In addition, the stately cherry paneled office offers privacy and a gorgeous built-in library. The upstairs features an 800+ sq ft master with fireplace, sitting room and custom California closets. Friends and family will feel like they’re at a B&B in any of the 4 inviting guest rooms, each with its own private bathroom. Relax in the media room, which offers a wall of built-ins and wine fridge. Even more, the 3,000 sq ft temp-controlled lower level offers endless opportunity to build a gym, workshop, wine cellar, bar – whatever you desire. Outside, a large deck and gazebo offer amazing privacy next to the 6+ acres of open space. An amazing bonus, you’re deeded to PVRA, a country-club-like facility for tennis, swimming and social events.
❮❯Closed$1,995,000 Closed- 5 bds
- 7 ba
- 10143 sqft
11 Turtle Ridge Court
Ridgefield, CT
Listing by: Annmarie Leonard - William Pitt Sotheby's Int'l -
Redding CT for Rent
Welcome to the Cottage on Portland! Beautiful Gardens & Totally private & serene yet just a few minute walk to Georgetown village shops, Train Station, restaurants, bars & more! This completely renovated gems boasts numerous updates to include central air, hardwood floors,energy efficient spray foam insulation new moldings and professional landscaping featuring five rooms plus a sunroom & partially finished basement all surrounded by gorgeous, thriving gardens in a fully-fenced yard. A bonus is you're surrounded by dozens of acres of protected woods, making you feel like you're in the middle of a lush forest. The home features hardwood floors and amazing gardens views from almost every room. Have you been searching for a rental with charm & style combined with a beautiful, private yard? Please schedule a visit, you'll love what you find!
❮❯Closed$3,150 Closed- 2 bds
- 1 ba
- 1021 sqft
60 Portland Avenue
Redding, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Ridgefield CT Home for Sale
Welcome Home to 76 Canterbury Lane in Ridgefield, CT! This breathtaking Colonial with charming front porch overlooking the rolling front grounds is impeccably maintained and quite simply the quintessential New England residence. The floor plan is well thought out with flowing rooms and brilliantly planned space. The center hall foyer is flanked by formal living and dining rooms, sunroom/billiards room drenched in sunlight, spacious kitchen and dining area ideally open to the family room and direct access to the deck. The main level is rounded out with the office and two powder rooms, and features 9' ceilings throughout plus exquisite millwork. The upper level offers the grand master suite with sitting area and gas fireplace, ensuite bath and walk-in closets, plus three additional bedrooms each with full bathrooms and ample closet space, spacious laundry room, and huge bonus room with walk-in closet perfect for playroom, guest space, studio, you name it. The unfinished lower level has extra high ceilings and framing with egress, ideal to finish or enjoy as a rec and exercise room. The property is smashing, absolutely picturesque and level, and located at the end of a quiet country road, teaming with sunlight and natural flora and fauna. Outstanding location with deeded rights to Pleasantview Recreational Association (pvra.org) and quick zip access to I-84 for various commutes, shopping including Trader Joe's and Whole Foods, and countless restaurants. Welcome Home!
❮❯Closed$1,749,000 Closed- 4 bds
- 5 ba
- 5564 sqft
76 Canterbury Lane
Ridgefield, CT
Listing by: Chip Neumann - Houlihan Lawrence -
Redding CT Home for Sale
Magnificent renovation of a Redding historic 1791 home on 2.11 rolling level acres. New 5/8" wood shingle roof 50 year lifetime warranty, copper flashing, new gutters and drainage. New clapboard cedar stained siding, new top of the line Marvin windows and doors. New 4 bedroom septic, new whole house air conditioning, new more efficient propane heating system, and all new plumbing. New oak flooring harvested from 100 year old black & red oak. New main level master bedroom suite with solid red oak floors, exquisite full bath, walk-in closet, dressing area, and french doors to huge bluestone patio. New kitchen with knotty Alder custom cabinetry, granite countertops, stainless steel appliances, and recessed lighting. Stunning new bathrooms, new laundry closet washer/dryer. Charming living room with remodeled new gas fireplace, mantle, and repointed chimney. New updated electrical panel, waterproof basement and neutocrete crawl space, spray foam insulation, new waterline to well, and new bilco doors. New walkways, stonewalls, Belgium block, side entrance with roof, and process laid prepped driveway. Additional front bluestone patio and stone walls on magnificent property with room for a pool. 3 outbuildings being sold as is.. Fantastic Bonus room 4th bedroom/office/rec room. Built in 1791 the Ebinezer Crofoot listed on the Redding historic homes list was originally built when George Washington was President! Exceptional restoration/ renovation is not to be missed!
❮❯Closed$750,000 Closed- 3 bds
- 3 ba
- 2353 sqft
73 Stepney Road
Redding, CT
Listing by: Debbie Chase-Jehu - William Pitt Sotheby's Int'l -
Danbury CT Home for Sale
The finest in luxury living at Poet's Landing on Candlewood Lake in Danbury! Freshly painted ground floor ranch with over 2450 sq. ft. open floor plan. Gourmet kitchen with granite countertops, Wolf range, Sub Zero refrigerator, morning breakfast bar. Dining room with slider to your patio which is suitable for grilling! Cozy living room with gas fireplace. Spacious hallways lead to: 1st bedroom; bathroom; 2nd bedroom is a junior suite; large den with a door; impressive extra large master bedroom suite with large walk-in closet with shelving, marble whirlpool bath, separate shower with glass enclosure. 1 car detached garage with pull-down stairs to attic storage. Amenities include heated outdoor pool with hot tub; fitness center; private sandy beach; large park-like grill area; fenced-in dog walk area; kayak racks available for rent next to launch area. A boat slip is reserved for this unit and is available for rent at adjacent Nina Marina.
❮❯Closed$695,000 Closed- 3 bds
- 3 ba
- 2465 sqft
16 Hayestown Road B106
Danbury, CT
Listing by: John Lewis - Howard Hanna Rand Realty -
Wilton CT Home for Sale
What better quality could you ask for in a home than one built by an established builder for himself and his family? Located on popular Wilton street, walking distance to scenic Kent Pond for skating and fishing, is this warm and inviting colonial. Built for the buyers of today, this home features classic details such as 9' ceilings, custom millwork and hard wood floors. Enjoy open living spaces which provide perfect flow for everyday living and entertaining. Gracious front foyer, living room w/ fireplace, and lovely dining room w/ tray ceiling for formal gatherings. The chef's eat-in kitchen is the heart of this home. Plenty of space for meal prep and conversation while gathering around the large island. Continue into the comfortable family room w/beautiful stone fireplace, coffered ceilings and wet bar. Desirable private home office w/ built ins are perfect for working from home and/or study. A huge mudroom w/ pantry, custom cubbies, 1/2 bath and drop dead brick floor complete the level. Second level includes bonus room, main bedroom suite w/gorgeous spa like bathroom and enormous walk in closet, 4 add'l ensuite bedrooms and laundry room. Special feature includes two add'l bedrooms, full bath and sitting/rec room on the third floor, Walk out lower level offers endless possibilities. Blue stone patio from the kitchen provides peaceful outdoor living. Level property, privacy, possible pool site. This is your opportunity to own a fabulous custom Polito built home!
❮❯Closed$1,725,000 Closed- 7 bds
- 7 ba
- 5507 sqft
165 Linden Tree Road
Wilton, CT
Listing by: Meghan Wall - Berkshire Hathaway NE Prop. -
Redding CT Home for Sale
A Classic New England cape located at the end of the cul de sac built by its owner for his family in 1967 is ready for its next owner. This home has a fantastic floor plan offering extensive living space 2,053 square feet complete with hardwood floors throughout both the first and second floors. A living room with a brick hearth fireplace and large windows providing lots of light. The dining room features a full wall of windows overlooking the property. The family room with a full wall of built-ins. is ready for gatherings. The kitchen has a breakfast bar, gas stove and plenty of cabinets and full size pantry. Off the back side of the kitchen is a 4 season 12x12 Sunroom. Second Floor-The master bedroom is nice and big 22x14 with large closets for plenty of storage. Two more bedrooms and a full bath share this level. The basement is full size at 900 Square feet with full ceiling height ready to be finished. Great location close to everything make this a great home. West Redding offers fabulous walking trails, the Mark Twain Library, concerts on the Green and many more cultural events, easy access to Metro Train North. shopping and dining.
❮❯Closed$535,000 Closed- 3 bds
- 2 ba
- 2053 sqft
12 Beauiles Lane
Redding, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Bethel CT Home for Sale
It is not often that upon approaching a home, you sense that it welcomes you with a hug. The very architecture of 4 Pell Mell Drive makes this a must see. You are drawn through the quaint brick courtyard to the front door, and once inside you will be bathed in light and delighted by the open and airy feel. The spacious, updated kitchen with tray ceiling and eating area is open to an intimate family room with vaulted ceiling and beautiful transom window where the morning sun pours through. Gorgeous hardwood floors lead to the open concept dining space and living room, featuring a 2-sided brick fireplace and windows with gorgeous sunsets views beyond the private, wooded backyard. Down the hallway you will find two lovely bedrooms served by a hall bath and a third ensuite bedroom with 3 closets. The main level living of the house continues to a primary suite with hardwood floors, 2 walk-in closets and a spacious full bath. The extensive lower level consists of a huge finished Rec room with oversized windows and doors to a brick patio & Hot tub, a pass-thru laundry room leads to a second large, fully finished area with a charming raised brick fireplace, oversized windows, a kitchenette and a full bath - perfect for in-law/au pair or gathering. The expansive backyard with mature landscaping is rimmed with woods for maximum privacy.
❮❯Closed$729,000 Closed- 4 bds
- 4 ba
- 3591 sqft
4 Pell Mell Drive
Bethel, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Bethel CT Home for Sale
Wow! Wait until you see this absolutely beautiful, move in ready, completely updated 1922 Colonial! Over 2,100 square feet with a wonderful open space concept blended with old world charm... expect the unexpected! Filled with natural light this home offers a main level with an inviting foyer, an expansive family room with gorgeous fireplace, beautiful hardwood floors and french doors to a slate patio, a spacious dining room with hardwood floors that flows into a lovely eat-in kitchen with stainless appliances and patio access - making for easy entertaining, and a powder room. The upper level consists of a primary suite with double closets, full bath with separate tub and shower and a sitting/office/4th bedroom, two additional bedrooms and hall bath. There is also a walk-up attic. A laundry room and ample storage space are found on the lower level and there is a one car garage. Sited on a half acre of private, professionally landscaped property bursting with flowering gardens. Conveniently located for a stroll to town, train, shops, restaurants and all that bucolic downtown Bethel has to offer.
❮❯Closed$575,000 Closed- 4 bds
- 3 ba
- 2169 sqft
78 Hoyts Hill
Bethel, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Redding CT Home for Sale
This meticulously maintained New England colonial is located on a picturesque, 2.73 level acres w/ park-like setting on a desirable cul de sac & just steps away from Joel Barlow High School. This pristine home offers 3,900sf on 3 finished levels, a Kingswood Cabinetry designed kitchen, hrwd floors, moldings & attached 2 car garage. The elegant entry foyer, formal living & dining rooms, library/office, & expansive kitchen w/ center island, granite counters & built in hutch, S/S appliances, hand forged hardware, dry bar, & sun filled breakfast room w / sliders leads to the rear first level deck to enjoy outside dining. The adjoining FR w/ fplc & grand ceiling, half bath/laundry complete the main floor. The second floor will continue to impress with luxurious MBR suite featuring plenty of natural light and space. The elegant private bath features Marble topped double vanity, soaking tub & separate shower. Enjoy three additional spacious bedrooms plus hall bath featuring a double vanity. The expansive lower level includes a fireplace, half bath, walk out sliders and plenty of windows. Through the sliders, enjoy the hot tub, grilling or playing in the beautiful back yard filled with specimen trees & plantings. Walk to the neighboring Joel Barlow tennis courts, turf fields, running & biking trails. This fantastic location is convenient to both Fairfield and Westport-13 miles and 62 miles to Grand Central Station. Upgrades-New roof-2011,Windows 2013,HVAC-2020 Well pump 2011 & more.
❮❯Closed$875,000 Closed- 4 bds
- 4 ba
- 3056 sqft
4 Cricklewood Road
Redding, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Redding CT for Rent
Welcome to the Cottage on Portland Ave in Redding! Beautiful Gardens & Totally private & serene yet just a few minute walk to Georgetown village shops, Train Station, restaurants, bars & more! This completely renovated gem boasts numerous updates to include central air, hardwood floors,energy efficient spray foam insulation new moldings and professional landscaping featuring five rooms plus a sunroom & partially finished basement all surrounded by gorgeous, thriving gardens in a fully-fenced yard. A bonus is you're surrounded by dozens of acres of protected woods, making you feel like you're in the middle of a lush forest. The home features hardwood floors and amazing gardens views from almost every room. Have you been searching for a rental with charm & style combined with a beautiful, private yard? Please schedule a visit, you'll love what you find! Best to see after 5:00pm tenets working from home.
❮❯Closed$3,150 Closed- 2 bds
- 1 ba
- 1021 sqft
60 Portland Avenue
Redding, CT
Listing by: Jay Contessa - William Pitt Sotheby's Int'l -
Fairfield CT Home for Sale
Climb the bluestone steps of this University area charmer and enjoy easy living! Sun streams in the front windows illuminating the spacious foyer and living room. Picture cozy gatherings by the fireplace or entertaining in the dining room. Shadowboxes accent the dining room walls which leads to both the eat-in kitchen or family room. The perfect place to unwind after a long day, the family room features hardwood floors, French doors to the backyard, and access to the powder room which has fresh tile, a pedestal sink and built-in shelving. The kitchen has an abundance of cabinet space, from the wall of pantry-like cabinets to the glass cabinetry. There is plenty of room for every chefs needs and easy access to laundry! A mudroom with cubbies and a bench is tucked neatly off of the kitchen and leads to the private backyard. Upstairs you will find four bedrooms and two full bathrooms. The primary suite has plenty of space to rest and relax, with a double vanity, walk-in shower and fabulous walk-in closet! Three additional bedrooms and a shared bathroom complete the second floor. Not to be missed, the finished lower level is perfect as a rec room, home office or storage. Outside, mature trees provide privacy and shade for the yard and patio. 329 Fairview Avenue is a quick walk to the neighborhood park, schools, downtown Fairfield, the train station and more! Move right in and call this beauty yours today.
❮❯Closed$859,000 Closed- 4 bds
- 3 ba
- 2460 sqft
329 Fairview Avenue
Fairfield, CT
Listing by: Sarah Pritchard Provenzano - William Raveis Real Estate -
Redding CT Home for Sale
Captivating & Serene! Welcome to 82 Drummer Lane - a beautiful, immaculate farmhouse style 4BR/2.5BA colonial that offers wonderful living spaces on 2 private acres. This quiet neighborhood loop is perfect for walking, biking and close to nearby hiking trails. Features include: Gleaming hardwood floors throughout, a double sided fireplace between the kitchen sitting room and the great room makes a cozy spot to enjoy time with family and friends. High ceilings in the kitchen, dining and great rooms add to the spaciousness of this lovely home. There are 3 ample sized bedrooms on the 2nd level (including the primary bedroom with full bath and walk-in closet) and a 4th bedroom (currently used as an office) on the main level. The lower level has a playroom that walks out to the backyard, a huge unfinished area for storage and mechanicals that leads out to a two car garage. Sit back and enjoy the sights and sounds of the woods through every season from the large deck, firepit area, lovely front yard or ground level patio! Don't miss this opportunity to live on one of Redding's most desirable streets!
❮❯Closed$675,000 Closed- 4 bds
- 3 ba
- 2745 sqft
82 Drummer Lane
Redding, CT
Listing by: Mary Phelps - William Pitt Sotheby's Int'l