Homes for Sale near Fairfield Country Day School

• 

  

  

  /38

  $2,065,000

  • 4 Beds
  • 3.5 Baths
  • 4,255 Sq Ft

  158 Coventry Ln, Fairfield, CT 06824

  Discover this Connecticut Colonial, now with a dramatic price improvement, nestled on a peaceful cul-de-sac. This gem sits on two acres of meticulously landscaped, flat grounds, free from wetlands, showcasing vibrant gardens, stone walls & bluestone walkways. Indulge in the heated saltwater pool and spa with a waterfall feature, and unwind in the inviting cabana/pool house. A full house generator

  Veronica Monahan Compass Connecticut, LLC

  158 Coventry Ln, Fairfield, CT 06824
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• 

  

  

  /39

  $1,475,000 Open Thu 10AM - 2PM

  • 5 Beds
  • 4.5 Baths
  • 3,086 Sq Ft

  259 Wilton Rd, Westport, CT 06880

  Discover the Westport lifestyle at its best. Set on nearly two private acres within walking distance of the Westport YMCA and Mahackeno trails, this spacious and flexible ranch feels like a private retreat yet remains close to town. With five bedrooms, four full baths, and an outdoor powder room off the garden patio, the home is designed for comfort and easy living. The main level features four

  Inna Agujen Coldwell Banker Realty

  259 Wilton Rd, Westport, CT 06880
• 

  

  

  /28

  $19,800,000

  • 8 Beds
  • 8.5 Baths
  • 9,995 Sq Ft

  Unlisted Address

  Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of

  Cyd Hamer William Pitt Sotheby's Int'l

  Unlisted Address
• 

  

  

  /40

  $715,000

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft

  333 Lenox Rd, Fairfield, CT 06825

  Beautifully renovated 2 family located on quiet side street 2 separate off street driveways. grassy level usable yard. Well done renovation: New roof with all new plywood, new gutters, new porch and attic windows. Surveyed April 2025. 2 new Navien combination heat and hot water units, new baseboards, 2 new electric service panels, new kitchens, new bathrooms, first floor has new washer dryer,

  Robert Richter Coldwell Banker Realty

  333 Lenox Rd, Fairfield, CT 06825
• 

  

  

  /30

  $659,900

  • 6 Beds
  • 3 Baths
  • 3,258 Sq Ft

  105 Fox St Unit 107, Bridgeport, CT 06605

  Great Black Rock legal two family home with a third floor accessory apartment conveniently located in walking distance to the Black Rock Train Station, Restaurants, Pubs, Music Venues, Waterfront Social Clubs, St. Mary's By The Sea and is minutes to I-95. The home is in very good condition and has been well maintained, the first and second floor units have very spacious rooms and the third floor

  John Kleps Berkshire Hathaway NE Prop.

  105 Fox St Unit 107, Bridgeport, CT 06605
• 

  

  /5

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  43 Helen St, Fairfield, CT 06824

  Fantastic in-town opportunity for builders and investors! On a tree lined street with the French bakery on the corner, this 2-family home is just 2 blocks to downtown Fairfield and the train and close to all 5 beaches! This 2-family home has been brought down to the studs inside and offers a blank canvas to bring your ideas to life. Currently setup as a 2-family, there are options to keep it a

  Carrie Sakey Coldwell Banker Realty

  43 Helen St, Fairfield, CT 06824
• 

  

  /19

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft

  125 Alexander Dr, Bridgeport, CT 06606

  North End Bridgeport Brick Two-Family - Fully Rented, Front & Back Units Investor-ready brick two-family located in Bridgeport's desirable North End. Features front and back unit layout-no shared walls-offering privacy and ease of access for tenants. The front unit is a 1-bedroom, 1-bath rented at $1,350/month, and the rear unit is a 2-bedroom, 1-bath rented at $1,500/month. Both leases are in

  Kristen Heinrich BHGRE Gaetano Marra Homes

  125 Alexander Dr, Bridgeport, CT 06606
• 

  

  /40

  $879,999 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,961 Sq Ft

  60 Winnepoge Dr, Fairfield, CT 06825

  Now's the perfect opportunity to own in the idyllic Lake Hills neighborhood-a sought-after enclave offering residents access to five private lakeside beaches! This thoughtfully renovated Cape Cod features a spacious floor plan ideal for entertaining. Its inviting facade & stunning new entryway create a warm welcome the moment you arrive. Inside, the new mudroom showcases high ceilings, stylish

  Andrea Viscuso Compass Connecticut, LLC

  60 Winnepoge Dr, Fairfield, CT 06825
• 

  

  /39

  $1,149,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  48 Sunset Rd, Easton, CT 06612

  Stylishly renovated 3BR, 2BA ranch in one of Lower Easton's most coveted neighborhoods! Set on .66 acres, this 1,748 sq. ft. home blends modern elegance with everyday ease. Sun-filled open layout showcases rich hardwood floors and a brand-new gourmet kitchen with quartz counters, stainless steel appliances, and upscale finishes-perfect for both casual dining and entertaining. The vaulted family

  Nicole Costantino Keller Williams Realty

  48 Sunset Rd, Easton, CT 06612
• 

  

  /29

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  140 Tunxis Hill Cut Off, Fairfield, CT 06825

  Stunning 3 bedroom, 2.5 bath home in the heart of Tunxis Hill! - This well updated colonial features a spacious living room with gas fireplace, and lots of natural light! - Gorgeous kitchen with quartz counters, subway tile backsplash, and stainless steel appliances! - Beautiful dining room with custom trim details - 9' ceilings & hardwood floors on the main level + crown molding throughout! -

  Todd Turcotte Milligan Realty.com

  140 Tunxis Hill Cut Off, Fairfield, CT 06825
• 

  

  /38

  $885,000

  • 4 Beds
  • 4 Baths
  • 2,521 Sq Ft

  28 Primrose Ln, Fairfield, CT 06825

  Welcome to 28 Primrose Lane. Drive up to this lovely home perched high on the corner with a beautiful outdoor setting of flowering perennial gardens, multiple rock gardens, woodland areas & flower beds loved by one family for more than 45 yrs. Main level features eat-in kitchen w/built in shelves/desk, D/R, L/R with French doors & great room w/high vaulted ceilings, painted wood beams and a floor

  Debra Carson William Raveis Real Estate

  28 Primrose Ln, Fairfield, CT 06825
• 

  

  /40

  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,648 Sq Ft

  53 Eastfield Terrace, Fairfield, CT 06825

  Filled with charm and curb appeal, this inviting 4-BR Colonial Split is perfectly sited on a quiet cul-de-sac just moments from Lake Mohegan's trails, playground, and beach. Original home was completely redesigned and expanded in 2010! A pretty front porch welcomes you home and sets the tone for the relaxed and comfortable vibe inside. Open main level features a spacious living room anchored by a

  Tracie and Vicki Team William Raveis Real Estate

  53 Eastfield Terrace, Fairfield, CT 06825
• 

  

  /22

  $700,000

  • 4 Beds
  • 3 Baths
  • 2,213 Sq Ft

  700 Laurel Ave, Bridgeport, CT 06604

  close to shopping centers, restaurants, and major highways. The first-floor unit was originally a two-bedroom, but it was converted into a one-bedroom. It can easily be changed back to a two-bedroom if needed. The second and third floors make up a large unit with three bedrooms and two full bathrooms. There's a living room, kitchen, office space, and one bedroom on the second floor. The other

  Sebastian Osorio Alpha Capital Realty, LLC

  700 Laurel Ave, Bridgeport, CT 06604
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  /17

  $4,400,000

  • 4 Beds
  • 5 Baths
  • 4,000 Sq Ft

  2117 Fairfield Beach Rd, Fairfield, CT 06824

  Welcome to Turning Point at Pine Creek, where the coastline bends to a point creating some of the most magnificent side-to-side sweeping views the Gold Coast has to offer. This very special beachfront site will offer Connecticut Home's latest architectural masterpiece. A 4000sf state of the art custom build with ultra high-end finishes which will no doubt be one of CT's most remarkable coastline

  Basil Amso RE/MAX Right Choice

  2117 Fairfield Beach Rd, Fairfield, CT 06824
• 

  

  /19

  $269,900

  • 2 Beds
  • 1.5 Baths
  • 1,260 Sq Ft

  236 Edgemoor Rd Unit D, Bridgeport, CT 06606

  Welcome to Fairfield Village! This townhouse style 2 bedroom, 1.5 bath unit on a cul-de-sac is just waiting for you! The townhouse offers an abundance of living space with living room, eat in kitchen/dining area, 1/2 bath on the main level, 2 generous size bedrooms and full bath on upper level along with a finished lower level adding additional living space for bedrooms, office, family room, etc.

  James Gerasi William Raveis Real Estate

  236 Edgemoor Rd Unit D, Bridgeport, CT 06606
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  /40

  $2,849,000

  • 5 Beds
  • 6 Baths
  • 4,142 Sq Ft

  40 Hermit Ln, Westport, CT 06880

  Set on more than two acres of exquisite, park-like property in the coveted Red Coat estate section of Westport, this spectacular modern home with a glorious gunite pool offers an ideal lifestyle. A designer's own residence, this home showcases uncompromising quality with intuitive features. The landscaped approach begins with a large stone parking court that accommodates entertaining on a grand

  Alex Chingas Coldwell Banker Realty

  40 Hermit Ln, Westport, CT 06880
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  /40

  $5,899,000

  • 7 Beds
  • 10 Baths
  • 11,036 Sq Ft

  9 Burr Farms Rd, Westport, CT 06880

  The home of your dreams that exceeds every expectation awaits at this spectacular, like-new residence built w/the finest quality & elevated design. Perfectly sited on one of Long Lots' top cul-de-sacs behind a stone wall, the manicured acre w/saltwater gunite pool/spa offers a serene backdrop for this exceptional property. The impressive, soaring foyer w/exquisite millwork introduces interiors w/

  Alex Chingas Coldwell Banker Realty

  9 Burr Farms Rd, Westport, CT 06880
• 

  

  /28

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 1,686 Sq Ft

  111 & 115 Old Easton Turnpike, Weston, CT 06883

  Welcome to this interior designer's personal residence, thoughtfully renovated in 2024 with luxurious, high-end finishes rarely found in a classic ranch-style home. Step inside to discover a brand-new quartz kitchen with custom cabinetry and millwork, a spa-inspired primary bathroom with double sinks, gorgeous tile and a walk-in shower, two additional beautifully renovated bathrooms, designer

  Joan Wright Compass Connecticut, LLC

  111 & 115 Old Easton Turnpike, Weston, CT 06883
• 

  

  /37

  $950,000

  • Land
  • 0.38 Acre
  • $2,500,000 per Acre

  489 Main St, Westport, CT 06880

  Build new or re-imagine what exists. Single Family with legal accessory apartment. New 5 bedroom septic system- just installed and new furnace and hot water heater in apartment. Let your imagination soar in creating your ideal situation. The main house and the accessory apartment each has a fireplace, The main house has 3 bedrooms and the apartment 2 bedrooms and each has 2 full baths. Hardwood

  Gabrielle DiBianco Higgins Group Bedford Square

  489 Main St, Westport, CT 06880
• 

  

  /39

  $649,000

  • 8 Beds
  • 4 Baths
  • 3,762 Sq Ft

  200 Harral Ave, Bridgeport, CT 06604

  Well-Maintained 4-Family Home - Ideal for Investors or Owner-Occupants! This income-producing property features four separate units, all in great condition. The layout includes two first-floor one-bedroom units and two upper-level three-bedroom units that span the 2nd and 3rd floors. Each first-floor unit offers a spacious living room, an eat-in kitchen with new appliances, a full bath, and an

  Lucy Larracuente-Johnson Larracuente & Johnson Realty, LLC

  200 Harral Ave, Bridgeport, CT 06604
• 

  

  /7

  $424,999

  • 4 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  241 Sampson St, Bridgeport, CT 06606

  North End diamond in the rough is just 1.4 miles from Sacred Heart University. New roof, siding, water heater, and main floor bathroom. This home has been in the same family since it was built in 1961 by another family member! Lower level features an apartment with separate bedroom, living room, partial kitchen, and full bath (which needs TLC) That space has its own walk out entrance. All large

  Janet Warren William Raveis Real Estate

  241 Sampson St, Bridgeport, CT 06606
• 

  

  /12

  $409,900

  • 4 Beds
  • 2 Baths
  • 1,224 Sq Ft

  65 Dobson St, Bridgeport, CT 06606

  Welcome to 65 Dobson, this charming Cape-style home is located in the sought-after North End of Bridgeport, offering 4 bedrooms and 2 full bathrooms. The main level features an eat-in kitchen with access to the backyard, a bright living room, two bedrooms, and a full bathroom with a skylight for added natural light. The upper level includes two additional bedrooms. The full basement is half

  Maura DeVellis Coldwell Banker Realty

  65 Dobson St, Bridgeport, CT 06606
• 

  

  /39

  $2,450,000

  • 5 Beds
  • 4.5 Baths
  • 4,318 Sq Ft

  400 Bronson Rd, Southport, CT 06890

  Discover refined waterfront living at 400 Bronson Road. A beautifully crafted custom colonial set along the peaceful Mill River in Southport. This elegant waterfront home offers five generously sized bedrooms, four and a half bathrooms, and over 4,000 square feet of thoughtfully designed space across four levels. High-end finishes and timeless design details shine throughout, from the white oak

  Charles Anello Douglas Elliman of Connecticut

  400 Bronson Rd, Southport, CT 06890
• 

  

  /12

  $78,000

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  21 Little St, Bridgeport, CT 06604

  Great opportunity to own and update your very own co-op home in the historic Seaside Village community of Bridgeport. This 1BR/1BA Townhouse offers a spacious eat-in kitchen, living room, bedroom, and full bath on the main level. Common charges include taxes, water, insurance, property management, plus the residents also enjoy access to a community garden! Located just minutes from Seaside Park

  Walter Carmona William Raveis Real Estate

  21 Little St, Bridgeport, CT 06604
• 

  

  /40

  $5,500,000

  • 6 Beds
  • 8 Baths
  • 9,601 Sq Ft

  10 Debra Ln, Westport, CT 06880

  Stunning 6 Bedroom 9600SF (including all 4 levels) Colonial in the heart of Westport. Built by Bluewater Home Builders, this stunning custom residence is situated on a private cul-de-sac in the central Hunt Club area. The traditional design boasts exceptional interior details, including soaring ceilings, beamed and coffered accents, shiplap paneling, and sleek millwork throughout all finished

  Linda Skolnick Coldwell Banker Realty

  10 Debra Ln, Westport, CT 06880
• 

  

  /39

  $349,900

  • 2 Beds
  • 1.5 Baths
  • 1,275 Sq Ft

  225 Edgemoor Rd Unit H, Bridgeport, CT 06606

  Come see this 3 level townhouse condo unit. 3 bedrooms and 2.5 baths. ready condition condition. Includes deeded parking.

  Ishwar Rameshar Besmatch Real Estate

  225 Edgemoor Rd Unit H, Bridgeport, CT 06606
• 

  

  /10

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,460 Sq Ft

  500 Dewey St, Bridgeport, CT 06605

  Please DO NOT DISTURB the occupant. Contact with occupants is prohibited. Opportunity to own a charming colonial-style home constructed in 1937. Offering over 1,400 square feet of living space, features 3 bedrooms and 1 full bathroom. This property includes the added benefit of off-street parking, ensuring ease and accessibility. Step outside into your own private fenced backyard ideal for family

  Jonathan Gineo Silver and Oak Realty

  500 Dewey St, Bridgeport, CT 06605
• 

  

  /3

  $4,395,000

  • 7 Beds
  • 7.5 Baths
  • 8,203 Sq Ft

  20 Morningside Dr S, Westport, CT 06880

  Embrace grandeur in this meticulously crafted 4-story estate. Over 8200 SQFT of Finished Living Space. The expansive first floor offers an open concept design-imagine seamless flow between the gourmet kitchen complete with a walk-in pantry, spacious living room, elegant dining room, and cozy family roomall warmed by the ambiance of three fireplaces. Upstairs, retire to the luxurious primary suite

  John Schiaroli Coldwell Banker Realty

  20 Morningside Dr S, Westport, CT 06880
• 

  

  /40

  $1,199,000

  • 5 Beds
  • 4.5 Baths
  • 3,154 Sq Ft

  90 White Oak Rd, Fairfield, CT 06825

  Welcome to 90 White Oak Rd, a custom-built Colonial in Fairfield's historic Brooklawn neighborhood. Adjacent to the Brooklawn Country Club, the property's .66 acres of lush lawn & mature trees create a serene and private setting. The 1st floor features an expansive front-to-back living room with a wood-burning fireplace, a sunroom with walls of windows, and screened-in porch. The formal dining

  Jennifer Peters William Raveis Real Estate

  90 White Oak Rd, Fairfield, CT 06825
• 

  

  /40

  $5,200,000 Open Sun 1PM - 3PM

  • 6 Beds
  • 9 Baths
  • 8,545 Sq Ft

  125 Old Rd, Westport, CT 06880

  Experience the elevated ease of modern luxury in this brand new SIGNATURE Home by SIR Development, Westport's most respected ground-up RE developer with 30+ years & 300+ completed homes. Set on a scenic park-like acre w/ gunite pool & circular drive, this move-in ready home avoids delays & financial uncertainty of a proposed new build. Conveniently located within walking distance of Long Lots

  Doug Bross Coldwell Banker Realty

  125 Old Rd, Westport, CT 06880
• 

  

  /14

  $155,000

  • 1 Bath
  • 629 Sq Ft

  80 Cartright St Unit 8B, Bridgeport, CT 06604

  Discover a rare opportunity to own a beautifully updated studio unit in Cartright Towers, a well-maintained building on the Fairfield/Bridgeport line. Whether you're an investor seeking strong rental potential or a buyer looking for a move-in ready home, this immaculate unit checks every box. Enjoy the convenience and security of full-time doorman service, plus amenities including elevators,

  Hillary Waite William Raveis Real Estate

  80 Cartright St Unit 8B, Bridgeport, CT 06604
• 

  

  /39

  $659,000

  • 5 Beds
  • 3 Baths
  • 4,098 Sq Ft

  45 Sampson St, Bridgeport, CT 06606

  Don't miss this exceptional two-family home located in the desirable North End of Bridgeport! Both units have been thoughtfully refreshed, offering a move-in ready experience for homeowners or tenants alike. The first floor includes five rooms with two bedrooms and one full bath, a spacious laundry room , a newly renovated white kitchen with stainless steel appliances, gleaming hardwood floors

  Kathie Sierras William Raveis Real Estate

  45 Sampson St, Bridgeport, CT 06606
• 

  

  /31

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft

  53 Hilltop Dr, Southport, CT 06890

  Welcome to 53 Hilltop Drive, a delightful Cape Cod-style home nestled on a quiet cul-de-sac in the heart of Southport, Connecticut. This lovingly maintained residence offers 3 spacious bedrooms, 2 full bathrooms, and 1,382 square feet of comfortable living space. Built in 1949, the home features classic hardwood floors, a partially finished basement, and an attached garage. The 0.26-acre lot

  Kaitlin Fulco Coldwell Banker Realty

  53 Hilltop Dr, Southport, CT 06890
• 

  

  /40

  $1,395,000

  • 4 Beds
  • 2.5 Baths
  • 2,384 Sq Ft

  117 Turney Rd, Fairfield, CT 06824

  Historic charm meets modern living! This beautifully updated 1919 Colonial blends timeless elegance with today's open concept design.4 bedrooms, 2.5 baths and 2,400sf include a stunning kitchen/dining area flowing into a Family room and columned side porch. Set on .28 acres with extensive gardens, you're just moments from Jennings Beach and the Marina. Fairfield Coastal Living at its finest.

  Sarah Keenan William Pitt Sotheby's Int'l

  117 Turney Rd, Fairfield, CT 06824
• 

  

  /30

  $3,100,000

  • 2 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  118 Roseville Rd, Westport, CT 06880

  A sexy modernist concrete retreat designed by Frank Lloyd Wright protege Francis Barry Byrne, this home is a masterwork of form, function, and sustainability. Thoughtfully built using the Golden Ratio, it sits high on a hill with panoramic views of ancient rhododendrons and oaks. Inside, limestone walls, minimalist lines, and warm natural light create a space that is both bold and serene. The

  Meredith Cohen Serhant Connecticut, LLC

  118 Roseville Rd, Westport, CT 06880
• 

  

  /8

  $469,000

  • 3 Beds
  • 1.5 Baths
  • 1,982 Sq Ft

  100 Lorraine St, Bridgeport, CT 06604

  Discover this beautifully maintained colonial-style single-family home, nestled in one of Bridgeport's most sought-after neighborhoods. This residence features spacious rooms filled with natural light, perfect for both relaxation and entertaining. The walk-out basement provides additional living space and easy access to the backyard, while the two-car garage ensures ample storage and convenience.

  Oswaldo Torres Las Americas Real Estate

  100 Lorraine St, Bridgeport, CT 06604
• 

  

  /29

  $249,600

  • 3 Beds
  • 1 Bath
  • 2,353 Sq Ft

  260 Birmingham St, Bridgeport, CT 06606

  Investor and contractor special! Welcome to 260 Birmingham Street, located in the heart of Bridgeport's North End. This property offers incredible potential for those looking to renovate and add value. Featuring 3 bedrooms and 1 bathroom across 1,601 sqft of living space, this home sits on a 0.11 acre lot and is just minutes from schools, shops, parks, and public transportation. The property is

  Teresa Bennett Sanchez Asset Realty

  260 Birmingham St, Bridgeport, CT 06606
• 

  

  /39

  $715,000

  • 9 Beds
  • 3 Baths
  • 3,249 Sq Ft

  31 Taft Ave, Bridgeport, CT 06606

  Investors take note. Legal 3 family with strong & stable rental income. North End. Close to Madison Avenue where all stores and dining are located. Convenient and great location. Long-term tenants with desire to continue staying.

  Jacqueline Yeap Keller Williams Prestige Prop.

  31 Taft Ave, Bridgeport, CT 06606
• 

  

  /29

  $950,000

  • 4 Beds
  • 2.5 Baths
  • 2,497 Sq Ft

  62 Soundview Ave, Fairfield, CT 06825

  Spectacular New Construction, 1/2 Duplex, part of a two unit Condo Complex, Each unit has 2497 sq ft & includes 4 BRS, 2 1/2 Baths & Finished Basement. Each unit features the following: 1st floor has an airy open floor plan w a seamless flow & soaring 9ft ceilings. The spectacular gourmet Kitchen has custom white painted cabinets & a large center island w quartz countertops. Stainless steel

  Mary Anne Lagana William Raveis Real Estate

  62 Soundview Ave, Fairfield, CT 06825
• 

  /2

  $25,000,000

  • 1 Bed
  • 1 Bath
  • 4,340 Sq Ft

  128 Beachside Ave, Westport, CT 06880

  6.62 acres of Long Island Sound waterfront property. A stunning modern architectural masterpiece. The structure is anchored by a 75 ft indoor pool and wall of seamless glass windows that feel connected to the water beyond , the single story structure also holds a kitchen, lounge and bath. The Red Barn is a secondary structure in the orchard section of the property - designed as an artist's studio

  Leslie Clarke Compass Connecticut, LLC

  128 Beachside Ave, Westport, CT 06880

Showing Results 41 - 80, Page 2 of 8